Organophotoredox-Catalyzed Decarboxylative C–O/N/S Bond Formation: Access to Ampakine APIs and Quinazolinone Alkaloids

This study describes a novel and general protocol featuring organophotoredox-catalyzed intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, and sulfur) bonds, enabling direct access to ampakine APIs (CX-614 and CX-554), quinazolinone alkaloids (deoxyvasicinone and mackinazolinone), and thiazinone scaffolds as well as their congeners with broad functional group tolerance and scalability. Mechanistic studies suggest a radical-polar crossover pathway via single-electron oxidation.

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Publication Details

Journal
Organic Letters
Published
2025-04-07
DOI
https://doi.org/10.1021/acs.orglett.5c00565
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Organophotoredox-Catalyzed Decarboxylative C–O/N/S Bond Formation: Access to Ampakine APIs and Quinazolinone Alkaloids

Sameer R. Sonavane, Gaurang J. Bhatt, Santosh B. Mhaske, Tushar B. Kale
2 citations
Organic Letters
Radical Photochemical Reactions
1.87
article

Organophotoredox-Catalyzed Decarboxylative C–O/N/S Bond Formation: Access to Ampakine APIs and Quinazolinone Alkaloids

Sameer R. Sonavane, Gaurang J. Bhatt, Santosh B. Mhaske, Tushar B. Kale
article en
2 citations

Abstract

This study describes a novel and general protocol featuring organophotoredox-catalyzed intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, and sulfur) bonds, enabling direct access to ampakine APIs (CX-614 and CX-554), quinazolinone alkaloids (deoxyvasicinone and mackinazolinone), and thiazinone scaffolds as well as their congeners with broad functional group tolerance and scalability. Mechanistic studies suggest a radical-polar crossover pathway via single-electron oxidation.

Organic LettersVol. 27(15)
National Chemical Laboratory (IN), Academy of Scientific and Innovative Research (IN)
University Grants Commission, Science and Engineering Research Board
Openalex Percentile: Top 17%
Radical Photochemical Reactions
1.87
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